3-<1-methyl-3-<1-methyl-3-(1-methyl-4-nitropyrrole-2-carboxamido)pyrazole-5-carboxamido>pyrazole-5-carboxamido>propionitrile | 177409-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-<1-methyl-3-<1-methyl-3-(1-methyl-4-nitropyrrole-2-carboxamido)pyrazole-5-carboxamido>pyrazole-5-carboxamido>propionitrile
• 英文别名: β-[1-methyl-3-[1-methyl-3-[1-methyl-4-nitropyrrole-2-carboxamido]pyrazole-5-carboxamido]pyrazole-5-carboxamido]propionitrile；N-(2-cyanoethyl)-2-methyl-5-[[2-methyl-5-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]pyrazole-3-carbonyl]amino]pyrazole-3-carboxamide
• CAS: 177409-23-3
• 化学式: C₁₉H₂₀N₁₀O₅
• 分子量: 468.432
• InChiKey: TVVRRWBDOAQFOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  198
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-<1-methyl-3-<1-methyl-3-(1-methyl-4-nitropyrrole-2-carboxamido)pyrazole-5-carboxamido>pyrazole-5-carboxamido>propionitrile 在 盐酸 、 氨 作用下， 生成 3-<1-methyl-3-<1-methyl-3-(1-methyl-4-nitropyrrole-2-carboxamido)pyrazole-5-carboxamido>pyrazole-5-carboxamido>propionamidine hydrochloride
  参考文献：
  名称：

  二霉素A的吡唑类似物的新型苯甲酰氮芥菜衍生物：合成和抗白血病活性。

  摘要：

  本文描述了新型双酚A的苯甲酸芥末（BAM）衍生物的设计和合成，该衍生物带有一个或多个吡唑环替代了后者的吡咯环。报道和讨论了针对L1210白血病的体外和体内活性。这些化合物中的一些表现出与塔莫司汀1相当的活性。与以BAM与吡咯相连的衍生物相比，所有带有靠近BAM部分的吡唑环的化合物均显示出降低的细胞毒性：发生时未观察到相同的作用在寡肽框架的idine末端。

  DOI：

  10.1016/s0968-0896(98)00205-3
• 作为产物：
  描述：

  {5-[5-(2-Cyano-ethylcarbamoyl)-1-methyl-1H-pyrazol-3-ylcarbamoyl]-1-methyl-1H-pyrazol-3-yl}-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 生成 3-<1-methyl-3-<1-methyl-3-(1-methyl-4-nitropyrrole-2-carboxamido)pyrazole-5-carboxamido>pyrazole-5-carboxamido>propionitrile
  参考文献：
  名称：

  Structure-activity relationship of novel tallimustine derivatives: synthesis and antitumor activity

  摘要：

  Oligopeptide-like derivatives structurally related to the antitumor agent tallimustine, where one or two pyrrole rings were replaced by pyrazole or thiazole rings and bearing benzoyl nitrogen mustard or bromoacryloyl moieties were synthesized and evaluated in vitro and in vivo against L1210 murine leukemia. Compounds 9 and 12 showed antitumor activity higher than or comparable with that of tallimustine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00205-3

文献信息

• Distamycin A analogues as antitumour or antiviral agents
  申请人：Pharmacia S.p.A.

  公开号：US05753629A1

  公开（公告）日：1998-05-19

  The present invention relates to compounds of formula (I) ##STR1## The compounds of the invention are useful as antitumor or antiviral agents.

  本发明涉及式(I)的化合物。##STR1##本发明的化合物可用作抗肿瘤或抗病毒剂。
• Cinnamoyl nitrogen mustard derivatives of pyrazole analogues of tallimustine modified at the amidino moiety: design, synthesis, molecular modeling and antitumor activity studies
  作者：Pier Giovanni Baraldi、Italo Beria、Paolo Cozzi、Cristina Geroni、Antonio Espinosa、Miguel A Gallo、Antonio Entrena、John P Bingham、John A Hartley、Romeo Romagnoli

  DOI：10.1016/j.bmc.2004.04.045

  日期：2004.7

  The design, synthesis and in vitro activities of a series of cinnamoyl nitrogen mustard pyrazole analogues of tallimustine 8-13, in which the amidino moiety has been replaced by moieties of different physico-chemical features are described, and the structure-activity relationships are discussed. In spite of the relevance of these modifications on the amidino moiety, these derivatives showed significant

  设计，合成和体外系列的塔木斯汀8-13的肉桂酰氮芥子吡唑类似物的设计，合成和体外活性，其中a胺部分已被具有不同理化特征的部分取代，并讨论了结构-活性关系。尽管这些修饰对a基部分具有相关性，但这些衍生物对小鼠白血病L1210细胞显示出显着的生长抑制活性。已经评估了一系列选择的化合物的序列选择性烷基化性质和对人K562白血病细胞的细胞毒性。因此，a基部分以及通常是碱性部分的存在不是生物学活性的绝对要求。
• DISTAMYCIN A ANALOGUES AS ANTITUMOUR OR ANTIVIRAL AGENTS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP0722446B1

  公开（公告）日：2002-12-11
• Novel benzoyl nitrogen mustard derivatives of pyrazole analogues of distamycin A: synthesis and antileukemic activity
  作者：Pier Giovanni Baraldi、Paolo Cozzi、Cristina Geroni、Nicola Mongelli、Romeo Romagnoli、Giampiero Spalluto

  DOI：10.1016/s0968-0896(98)00205-3

  日期：1999.2

  The design and synthesis of novel benzoic acid mustard (BAM) derivatives of distamycin A bearing one or more pyrazole rings replacing the pyrrole rings of the latter are described. In vitro and in vivo activities against L1210 leukemia are reported and discussed. Some of these compounds show an activity profile comparable to tallimustine 1. All the compounds bearing the pyrazole ring close to the BAM

  本文描述了新型双酚A的苯甲酸芥末（BAM）衍生物的设计和合成，该衍生物带有一个或多个吡唑环替代了后者的吡咯环。报道和讨论了针对L1210白血病的体外和体内活性。这些化合物中的一些表现出与塔莫司汀1相当的活性。与以BAM与吡咯相连的衍生物相比，所有带有靠近BAM部分的吡唑环的化合物均显示出降低的细胞毒性：发生时未观察到相同的作用在寡肽框架的idine末端。
• Structure-activity relationship of novel tallimustine derivatives: synthesis and antitumor activity
  作者：Pier Giovanni Baraldi、Italo Beria、Barbara Cacciari、Laura Capolongo、Paolo Cozzi、Nicola Mongelli、Romeo Romagnoli、Giampiero Spalluto

  DOI：10.1016/0960-894x(96)00205-3

  日期：1996.6

  Oligopeptide-like derivatives structurally related to the antitumor agent tallimustine, where one or two pyrrole rings were replaced by pyrazole or thiazole rings and bearing benzoyl nitrogen mustard or bromoacryloyl moieties were synthesized and evaluated in vitro and in vivo against L1210 murine leukemia. Compounds 9 and 12 showed antitumor activity higher than or comparable with that of tallimustine. Copyright (C) 1996 Elsevier Science Ltd